Dye & Durham DND-T has appointed its fifth chairperson in less than a year as well as an interim chief executive officer, as the chronically governance- and debt-challenged legal software company’s stock continues to plumb record lows.
The Toronto company said Monday that chair Mary Filippelli, who joined the board in May, had stepped down for unspecified reasons. She is being replaced as chair by Angela Zhang, a private equity investor from New York, who joined the board in March.
Ms. Filippelli and Ms. Zhang were members of a D&D board transformation committee, along with one-time chairman Tyler Proud, that took command of the company in June. The committee was struck to replace ousted chief executive officer George Tsivin. As head of the transformation committee, Mr. Proud, the brother of former CEO Matt Proud, effectively led D&D through the summer.
2025: Another board overhaul caps off year of chaos for beleaguered Dye & Durham
Chief operating officer Todd Schulte, who joined D&D this year, has taken over as interim CEO and the transformation committee has been dissolved effective immediately.
D&D stock has cratered by 94 per cent in the past year, slipping below $1 for the first time in late July. It closed at an all-time low of 68 cents on Friday. The stock last topped $50 a share in June, 2021. In June, before Mr. Tsivin’s departure, S&P Global Ratings cut its junk rating on the company by a notch to CCC+ owing to its “unsustainable capital structure,” the agency said in a research report. S&P noted that D&D’s adjusted leverage-to-operating earnings had risen in March to 9.5 times its operating earnings, indicating a worsening level of indebtedness relative to the company’s ability to cover its obligations. That compares with 8.3 times in June, 2025.
In a recent message to staff, Tyler Proud said the transformation committee had assumed leadership when D&D “was at a difficult point. We needed to bring stability to the business, rebuild the leadership team and establish a clear operating direction. Important decisions had to be made quickly, and there was no time to stand still.”
In the memo, obtained by The Globe and Mail, Mr. Proud said that on the committee’s watch, D&D had rebuilt its executive team, accelerated its cost reduction program, and built “a detailed bottom-up budget that provides a clear path for the company to remain within its financial covenants over the coming year,” among other moves.
“There is still much to do, but the company is in very good hands,” he wrote. Mr. Proud did not respond to a request for comment.
Mr. Proud, one of the company’s largest shareholders, was D&D chairman before it went public in mid-2020. He and a group of other shareholders that grew disaffected by the company’s governance and his brother Matt Proud’s leadership after a debt-fuelled acquisition binge. Those investors, including PenderFund Capital Management Ltd. – which dumped its remaining shares this year at a loss – supported an activist campaign led by New York’s Engine Capital Management LP in 2024 that forced Matt Proud’s exit and a board overhaul. Tyler Proud was also involved in the hiring of Mr. Tsivin.
Dye & Durham names Mary Filippelli as new board chair
But the Engine board failed to deliver quick changes as promised, results disappointed and the company was hit with a cease-trading order after it was late filing audited financial statements last year.
Mr. Proud turned on the Engine-led board last fall with a proxy challenge. That prompted the departure of Engine founder and D&D chair Arnaud Ajdler and the appointment of several directors Mr. Proud had proposed. He later soured on Mr. Tsivin as well. Bay Street veteran Alan Hibben became chairman for a few weeks last fall but was replaced by fellow director Eddie Smith. Mr. Smith left the board in late May, followed soon after by Mr. Hibben. Both left in June.
The latest changes follow other recent setbacks. D&D reported sharply lower revenues, operating profits and cash flows in May, and the board quietly shelved a sales process for the whole company after receiving two preliminary bids earlier this year. D&D is still considering offers for its financial services unit and the strategic process remains ongoing.
Ms. Zhang said in a statement “the Board remains confident that with consistent execution across our product portfolio and markets, Dye & Durham can deliver meaningful value for all of its shareholders.”